Benzene derivative
a technology of benzene derivatives and derivatives, applied in the field of benzene derivatives, can solve the problems of a large number of nerves at the same time, a single nerve may be damaged, and a large number of nerves may be damaged simultaneously, so as to achieve the effect of potent nerve-protecting and/or-repairing activity
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example 1
3-(2-hydroxyphenyl)propanoate
[0264]Sulfuric acid (0.26 mL) was added to a solution of 3,4-dihydrocoumarin (50.0 g) in isopropyl alcohol (500 mL), and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under a reduced pressure, and the resultant residue was diluted with ethyl acetate. The solution was washed with a saturated aqueous sodium bicarbonate solution, water and saturated saline, was then dried over sodium sulfate, and was then concentrated under a reduced pressure. In this manner, the title compound (73.2 g) having the physical property values shown below was produced.
[0265]1H-NMR (CDCl3): δ 1.20, 2.66-2.70, 2.87-2.91, 4.95-5.08, 6.86-6.91, 7.06-7.15, 7.35.
example 2
3-(2-(2-(1,3-dioxan-2-yl)ethoxy)phenyl)propanoate
[0266]Potassium phosphate (2.85 g) was added to a solution of the compound produced in Example 1 (2.00 g) and 2-(2-bromoethyl)-1,3-dioxane (2.43 g) in DMF (4 mL), and the reaction mixture was stirred at 70° C. for 2 hours. The reaction mixture was poured into 1 M hydrochloric acid, and the resultant solution was extracted with ethyl acetate. An organic layer was washed with water and saturated saline, was then dried over sodium sulfate, and was then concentrated under a reduced pressure. The resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→4:1). In this manner, the title compound (2.73 g) having the physical property value shown below was produced.
[0267]TLC: Rf 0.57 (hexane:ethyl acetate=2:1).
example 3
3-(2-(3-oxopropoxy)phenyl)propanoate
[0268]A solution of the compound produced in Example 2 (500 mg) and lutidine (0.40 ml.) in dichloromethane (1.5 mL) was cooled to −15° C., and trimethylsilyltrifluoromethanesulfonate (0.42 mL) was added to the solution. The resultant reaction mixture was stirred at 0° C. for 2 hours. Ice (10 g) was added to the reaction solution, and the resultant solution was stirred at 0° C. for 15 minutes. Water and ethyl acetate were added to the solution, the resultant solution was stirred at 0° C. for 20 hours, the resultant reaction mixture was poured into 1 M hydrochloric acid and ethyl acetate, and the resultant solution was extracted with ethyl acetate. An organic layer was washed with water and saturated saline, was then dried over sodium sulfate, and was then concentrated under a reduced pressure. In this manner, the title compound (443 mg) having the physical property values shown below was produced.
[0269]1H-NMR (CDCl3): δ 1.20, 2.50-2.55, 2.93-2.96, ...
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